Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst †

Chiral amines are one of the ubiquitous functional groups in fine chemical, pharmaceutical and agrochemical products, and the most convenient, economical, and eco-benign synthetic pathway to these amines is direct asymmetric reductive amination (DARA) of prochiral ketones. This paper shows that a wi...

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Detalles Bibliográficos
Autores principales: Villa-Marcos, Barbara, Li, Chaoqun, Mulholland, Keith R., Hogan, Philip J., Xiao, Jianliang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257260/
https://www.ncbi.nlm.nih.gov/pubmed/20428055
http://dx.doi.org/10.3390/molecules15042453
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author Villa-Marcos, Barbara
Li, Chaoqun
Mulholland, Keith R.
Hogan, Philip J.
Xiao, Jianliang
author_facet Villa-Marcos, Barbara
Li, Chaoqun
Mulholland, Keith R.
Hogan, Philip J.
Xiao, Jianliang
author_sort Villa-Marcos, Barbara
collection PubMed
description Chiral amines are one of the ubiquitous functional groups in fine chemical, pharmaceutical and agrochemical products, and the most convenient, economical, and eco-benign synthetic pathway to these amines is direct asymmetric reductive amination (DARA) of prochiral ketones. This paper shows that a wide range of aliphatic ketones can be directly aminated under hydrogenation conditions, affording chiral amines with good to excellent yields and with enantioselectivities up to 96% ee. The catalysis is effected by the cooperative action of a cationic Cp*Ir(III) complex and its phosphate counteranion.
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spelling pubmed-62572602018-11-30 Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst † Villa-Marcos, Barbara Li, Chaoqun Mulholland, Keith R. Hogan, Philip J. Xiao, Jianliang Molecules Article Chiral amines are one of the ubiquitous functional groups in fine chemical, pharmaceutical and agrochemical products, and the most convenient, economical, and eco-benign synthetic pathway to these amines is direct asymmetric reductive amination (DARA) of prochiral ketones. This paper shows that a wide range of aliphatic ketones can be directly aminated under hydrogenation conditions, affording chiral amines with good to excellent yields and with enantioselectivities up to 96% ee. The catalysis is effected by the cooperative action of a cationic Cp*Ir(III) complex and its phosphate counteranion. Molecular Diversity Preservation International 2010-04-08 /pmc/articles/PMC6257260/ /pubmed/20428055 http://dx.doi.org/10.3390/molecules15042453 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Villa-Marcos, Barbara
Li, Chaoqun
Mulholland, Keith R.
Hogan, Philip J.
Xiao, Jianliang
Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst †
title Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst †
title_full Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst †
title_fullStr Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst †
title_full_unstemmed Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst †
title_short Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst †
title_sort bifunctional catalysis: direct reductive amination of aliphatic ketones with an iridium-phosphate catalyst †
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257260/
https://www.ncbi.nlm.nih.gov/pubmed/20428055
http://dx.doi.org/10.3390/molecules15042453
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